Taylor Swift is Doing A Thing, So Here Are the 25 Best Taylor Swift Songs

After erasing her entire web presence last Friday, Taylor Swift spent the first half of this week revealing a snake/serpent before announcing that her new single would be released THIS THURSDAY and the her sixth studio album, Reputation, would be dropping in November. She is taking a page out of RuPaul’s Drag Race contestant Alaska Thunderfuck’s book, and reclaiming the snake emoji. Since ubiquity seems imminent for everyone’s problematic fav, the timing couldn’t be better for a dive into her career up to this point.
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25. “Teardrops On My Guitar” — Taylor Swift
The standout single from Taylor’s debut album, this track is the perfect example of how even when she was establishing her country roots, there was evidence of pop-crossover potential and ambitions. I have one question though…does “Drew” get royalties for this?
24. “Haunted” — Speak Now
This track is probably Taylor’s only song that I would say reminds me of something composed by Clint Mansell. The orchestration is really epic here, and it adds a lot of power to what could otherwise be a run of the mill Taylor Swift breakup song.
23. “White Horse”
22. “You’re Not Sorry” — Fearless
These two ballads from Fearless showed early some of Taylor’s prowess for a good breakup song. Side note: remember when Tay cameo’d on CSI? And there was a CSI remix of “You’re Not Sorry”? YEAH.

21. “State of Grace”
20. “Holy Ground” — Red
These two tracks from Red are HIGHLY underrated. They don’t have all of the flash of the singles from the album or the emotional pull of the ballads, but they are fun! In both instances we get mature reflections on the end of a relationship that aren’t meant to be cheeky and aren’t meant to gut us, which to this point had been Swift’s specialty.
19. “Welcome to New York” — 1989
The prologue for 1989 as an album and a tour, sets the stage for what would become a tour de force in pop music excellence. Dare I say it left me wanting to dance to this beat…forevermore?
18.“The Last Time” featuring Gary Lightbody of Snow Patrol — Red
This duet was part of a triad of heartbreaking, knock-down, drag-out, breakup jams featured on Red. You say it’s the last time, but you KNOW your dumbass will find yourself in a taxi/lyft/uber to your ex’s place.
17. “This Love”
16.“You Are In Love” — 1989
These two ballads from 1989 are both so good, and both show distinct influence from collaborator, Jack Antonoff. They were vastly overlooked amongst the plethora of pop perfection they were hidden between.
15. “I Almost Do” — Red
Another one of the three great Red breakup jams, this one is about resisting the urge to call the ex to see if you should just dive right back into it because WHAT COULD GO WRONG!
14. “Style” — 1989
This song is Swift at just…just her coolest, you know? It’s a very confident song about two people who know that they are attractive and who are too cool to see the red flags being flown.
13. “Love Story” — Fearless
William Shakespeare who? Ms. Swift wasn’t a fan of the outcome of Romeo & Juliet, and decided everything between to the two houses, both alike in dignity, could just be smoothed over by a conversation between Romeo and Mr. Capulet. When will your fav rewrite Shakespeare? Iconic.
12. “New Romantics” — 1989
This bonus track from the Target deluxe edition of 1989 had no business being so good. This jam was the soundtrack to many a pregame for those in the know, and for what it’s worth I bet it was Lorde’s favorite track on the album.
11. “Red” — Red
The Red title track features some very basic lyrics, using colors to evoke the emotions of a break up. It’s really simple, but it works and sets the scene for the rest of the album that follows.
10. “You Belong With Me” — Fearless
*Insert I’m really happy for you and Imma let you finish… joke here* This song was a part of the moment that made Taylor Swift famous, and led to a YEARS long feud with Kanye West, amongst others. There’s something sort of reassuring about knowing that celebrities live for messy drama. Any way, this song is cute for early Taylor.
9. “I Knew You Were Trouble.” — Red
“Trouble” saw our girl trying on some of the EDM dubs that were really big in 2012 and it largely worked. Her overly serious video (below)? Eh…it was clear she was going for something like what Lana Del Rey and Rihanna were doing at the time. This song was very 2012. This song was huge.
8. “Shake It Off” — 1989
Look up “bop” in the dictionary, and you’re likely to find “Shake It Off” by Taylor Swift. She hit us with the horns right before Meghan Trainor hit us over the heads with the horns (r.i.p. the horns). This is a song for people who like fun!
7. “22” — Red
Imagine for a moment, if you will, Taylor Swift released “22” in the summer of 2017. The pure escapism on display in this song would have been SO well received by a country/world looking to get away from the constant barrage of bad news. Also, it’s just a bop!
6. “Bad Blood” featuring Kendrick Lamar — 1989
This song and video proved to be lightning rods for several of Swift’s most prominent beefs over the years. The song is a pointed jab at Katy Perry, and the video was nominated for Video of the Year at the VMAs, while Nicki Minaj’s “Anaconda” video was not. Taylor and Kendrick ultimately won that award, but not before Taylor ate her words in an exchange with Nicki, and they publicly buried the hatchet to open that year’s VMAs. Regardless of all that drama, this song is a jam.
5.“Mine” — Speak Now
The story told in “Mine” ultimately could never play out as written for Swift now, but it’s a story of a couple with modest means just making it work. It’s a really great song about the mechanics of committing to a long term relationship, and I would say it’s her very best love song.
4. “We Are Never Ever Getting Back Together” — Red
This song was EVERYWHERE. The cutesy, quirky music video and the laughable singalong chorus did a lot to pivot Taylor toward full-time international pop superstar.
3. “Out of the Woods” — 1989
This song, like most of 1989, has been torn through for the gossipy details it features about Taylor’s relationship with Harry Styles. In this instance, a lot of the specifics work as really interesting metaphors for the ending of a doomed romance.
2. “All Too Well” — Red
If you’ve been through a breakup since Fall 2012, and you haven’t found yourself cry-scream-singing along to “All Too Well,” you! are! doing! it! wrong! In one of her most well-written songs to date, Swift takes the details of what has to be her relationship with Jake Gyllenhaal, and makes a song that captures the universal feeling of being “okay but not fine at all” about a relationship cut short by mismatched expectations.
- “Blank Space” — 1989
This song is a confection of pop music bliss, and it is Taylor Swift at her very best. Full-blown self awareness, flipping the manic-pixy-dream-girl trope on it’s head and reclaiming her perception as someone with a “long list of ex-lovers” that’ll tell you she’s insane. The video is Swift at her campiest yet. We can only hope there is more of this iteration of Taylor Swift to come in the Reputation era.
